SCHEDULED MAINTENANCE
Oxidation of anthracene with cerium(IV) ammonium nitrate
Abstract
The oxidation of anthracene with cerium(IV) ammonium nitrate appears to occur through an initial anthracene radical cation which is transformed into a transient anthrol nitrate. Homolysis of the oxygen–nitrogen bond of the anthrol nitrate furnishes the nitrite radical and a mesomeric anthrone radical. While the former attacks the initial ion radical with a concerted mechanism to yield anthrol nitrite, the latter undergoes dimerisation to bianthrone, addition of a nitrate radical to yield 9,10-dihydro-10-oxo-9-anthryl nitrate which subsequently disproportionates to anthraquinone and nitrous acid, and oxidation to the anthrone cation. This is attacked by a nucleophile to yield 10-methoxyanthrone or 10-acetoxyanthrone according to the solvent used.
Please wait while we load your content...
